4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies
Nine 2-(1,2-benzothiazol-3-yl)-N-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)propanamides combining a benzisothiazole and 4-thiazolidinone in one framework were designed and synthesized. The aim of the study was to verify their effectiveness to affect the inflammatory/oxidative process in which free oxygen...
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MDPI AG
2018-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/2/415 |
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doaj-5856ce1354284cb7a6722e537e31437d2020-11-24T20:57:59ZengMDPI AGMolecules1420-30492018-02-0123241510.3390/molecules23020415molecules230204154-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking StudiesMatteo Incerti0Lucia Crascì1Paola Vicini2Esin Aki3Ismail Yalcin4Tugba Ertan-Bolelli5Venera Cardile6Adriana Carol Eleonora Graziano7Annamaria Panico8Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, ItalyDepartment of Drug Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, ItalyDepartment of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, ItalyPharmaceutical Chemistry Department, Faculty of Pharmacy, Ankara University, Tandogan, Ankara 06100, TurkeyPharmaceutical Chemistry Department, Faculty of Pharmacy, Ankara University, Tandogan, Ankara 06100, TurkeyPharmaceutical Chemistry Department, Faculty of Pharmacy, Ankara University, Tandogan, Ankara 06100, TurkeyDepartment of Physiological Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, ItalyDepartment of Physiological Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, ItalyDepartment of Drug Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, ItalyNine 2-(1,2-benzothiazol-3-yl)-N-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)propanamides combining a benzisothiazole and 4-thiazolidinone in one framework were designed and synthesized. The aim of the study was to verify their effectiveness to affect the inflammatory/oxidative process in which free oxygen and nitrite (ROS and RNS) radicals, inflammatory mediators, such as nuclear factor κB (NF-κB), and matrix metalloproteinases (MMPs) are involved. Docking studies of all the compounds were performed in order to explore their binding mode at the MMP-9 protein. An appreciable anti-inflammatory/potential wound healing effects of the tested compounds was highlighted. Derivative 23, bearing a 4-carboxyphenyl substituent at C2 of the 4-thiazolidinone ring, exhibited the highest activity, being able to inhibit MMP-9 at nanomolar level(IC50 = 40 nM).http://www.mdpi.com/1420-3049/23/2/4154-thiazolidinonesORAC assaymetalloproteinase-9docking studykeratinocytes culturesnuclear factor-κB |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Matteo Incerti Lucia Crascì Paola Vicini Esin Aki Ismail Yalcin Tugba Ertan-Bolelli Venera Cardile Adriana Carol Eleonora Graziano Annamaria Panico |
| spellingShingle |
Matteo Incerti Lucia Crascì Paola Vicini Esin Aki Ismail Yalcin Tugba Ertan-Bolelli Venera Cardile Adriana Carol Eleonora Graziano Annamaria Panico 4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies Molecules 4-thiazolidinones ORAC assay metalloproteinase-9 docking study keratinocytes cultures nuclear factor-κB |
| author_facet |
Matteo Incerti Lucia Crascì Paola Vicini Esin Aki Ismail Yalcin Tugba Ertan-Bolelli Venera Cardile Adriana Carol Eleonora Graziano Annamaria Panico |
| author_sort |
Matteo Incerti |
| title |
4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies |
| title_short |
4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies |
| title_full |
4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies |
| title_fullStr |
4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies |
| title_full_unstemmed |
4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies |
| title_sort |
4-thiazolidinone derivatives as mmp inhibitors in tissue damage: synthesis, biological evaluation and docking studies |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2018-02-01 |
| description |
Nine 2-(1,2-benzothiazol-3-yl)-N-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)propanamides combining a benzisothiazole and 4-thiazolidinone in one framework were designed and synthesized. The aim of the study was to verify their effectiveness to affect the inflammatory/oxidative process in which free oxygen and nitrite (ROS and RNS) radicals, inflammatory mediators, such as nuclear factor κB (NF-κB), and matrix metalloproteinases (MMPs) are involved. Docking studies of all the compounds were performed in order to explore their binding mode at the MMP-9 protein. An appreciable anti-inflammatory/potential wound healing effects of the tested compounds was highlighted. Derivative 23, bearing a 4-carboxyphenyl substituent at C2 of the 4-thiazolidinone ring, exhibited the highest activity, being able to inhibit MMP-9 at nanomolar level(IC50 = 40 nM). |
| topic |
4-thiazolidinones ORAC assay metalloproteinase-9 docking study keratinocytes cultures nuclear factor-κB |
| url |
http://www.mdpi.com/1420-3049/23/2/415 |
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